Hydrochloric Acid → HCID 22885996, compound

HRID 375516Notes

Reaction equation

HRID 375516 reaction equation
[NH2:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[CH2:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[O:22][CH:23]1[CH2:25][CH2:24]1.C(OCC)(=O)C.[ClH:32]>O1CCOCC1.CCCCCC>[ClH:32].[NH2:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[CH2:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[O:22][CH:23]1[CH2:24][CH2:25]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 9906121HCID 9906121, compound

Product 1

HCID 22885996HCID 22885996, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve 4-Amino-17β-(cyclopropyloxy)androst-4-en-3-one into ethyl acetate (20 mL) and treat with 4M hydrochloric acid in dioxane (about 2 mL). Remove the solvent on a rotary evaporator. Titrate the resulting solid with ethyl acetate to give a gelatinous material and heat in a steam bath until a solid separates. Cool the mixture to room temperature and dilute with an approximately equal portion of hexane. Filter the solid and wash in ethyl acetate:hexane (1:1) and dry to obtain the title compound. IR(KBr) ν 2675, 1662, 1641 cm-1. MS(CI) 344 (100%, M+1), 286(30%, M+1, cyclopropyl-OH) 1H-NMR(CDCl3) 0.38-0.61 (4H, m, 2×CH2), 0.79(3H, s, C18 -Me), 1.25 (s, C19 -Me), 3.24 (1H, m, cyclopropyl-H), 3.42(1H, t, C17), 9.74(2H, v.br., NH.HCl). Anal. calc'd for C22H34ClNO2 : C: 69.54, H: 9.02, N:3.69; Found: C:69.06, H: 8.89, N:3.94.

Workup

  1. customRemove the solvent
  2. customon a rotary evaporator
  3. customto give a gelatinous material
  4. temperatureheat in a steam bath until a solid separates
  5. filtrationFilter the solid
  6. washwash in ethyl acetate:hexane (1:1)
  7. customdry

Sources & evidence

ORD record
ord-e47af854a187475680edd587765c4fac
Source dataset
uspto-grants-1996_01
Patent number
US05486511

Reaction notes

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